Azo dyes



Patented May 3, 1938 AZO DYES Chester w. Hannum and Swanie s. Rossander, Wilmington, DeL, assig'nors to E. I. du Pont de Nemours & Company, W

ilmington, Del., a.

corporation of Delaware No Drawing. Application July 8, 1937,

Serial No. 152,527

4 Claims.

This invention relates to blue and violet dyes of the azo class and 'to means of producing and applying them.

The prior art discloses blue and violet dyes of a type bearing a superficial similarity to the dyes of this invention. In German Patent 163,321 (1905), for example, are dyes which have fair utility but are lacking in sufllcient fastness to washing, whereby the utility is greatly diminished.

It is an object of this invention to produce new dyes of blue and violet shades which have exceptional fastness to washing and which are also fast to light, heat, chlorine, and the other infiuences which aflect the permanence of dyes.

The objects 01' the invention are attained, generally speaking, by manufacturing and applying to the fiber by development thereon the class of colors represented by the formula:

in which aryl is one of the group consisting of benzene and alpha naphthylamine and in which at least one aryl" has a water-solubilizing substituent, E has a single nucleus from the group consisting of benzene and phenyl-pyrazolone, Z has a single nucleus from the group consisting of beta-naphtha], phenyl-pyrazolone, meta-' tolylene-diamine, and acetoacet-arylide, and Y is one or more of the group consisting of hydrogen, alkyl, alkoxy, halogen, carboxy, and sulfonic acid.

The dye is applied to the fiber by directidyeing S OrNB N=N N=1-l OaNa . i 0mg.

(Cl. 8-5) with a dyestuil! represented in'the form ofit free acid by the formula:

I Y Y Y in which aryl is one of the group consisting of benzene and alpha-naphthylamine, at least one of the said aryls having a water-solubilizing group from the class consisting of carboxylic acid I and sulionic acid, E is one of the group consisting of benzene and phenyl pyrazolone, having a free amino group, and Y is at least one of the I group consisting of hydrogen, alkyl, alkoxy, and halogen, diazotizing and developing with betanaphthol, preferably, or with phenyl-pyrazolone, acetoacet-arylide, and meta-tolylene-diamine, or with a benzene or naphthalene compound capable of coupling.

The following examples illustrate the invention but do not limit it.

twentieth part of caustic soda. Stir the solution rapidly while adding the above rinsed piece goods. Rinse in cold water and dry. The probable Stir for 15 minutes. The dyeing is a blue shade. formula of the dye on the iiber is:

Diem component Glevu acid-4 naphthyiamine l,6 Oleves acid-r -naphthyiamine-)l,6 Cieves ldd-) Cloves acid-e Cleves acid-e Cloves acid- 1, G-Cleves In the foregoing tablethe arrows mean coupled by the diazo reaction. These colors have excellent shades of blue and violet and outstanding fastness to washing and outstanding discharge properties. They are also fast to the usual destructive influences and accordingly are superior colors.

At least one of the center nuclei must contain a water-solubiiizing group, such as suifonic or'carboxylic acid and two such groups are often of assistance. Each of the aryl nuclei may also contain one or more substituents from the group consisting of hydrogen, halogen, alkyl, alkoxy,

carboxy. and sulfonic acid.

As many apparently widely diiierent embodiments of. this invention may be made without departing from the spirit and scope thereof, it is to be understood that we do not limit overselvcs to the specific embodiments thereof except as defined in the appended claims.

We claim:

1. The compound represented in the form of its sodium salt by the formula:

BOaNa OsNl 2. The compound'represented in the form of its free acid by the formula:

in which a l is one of a group consisting of benzene and aipha-naphthylamine, E has a single arrests Shade cellulose Coupling component -naphthyiamine i,6-Olevee acid--) Beta-nsphthoi Blue.

. Vioiet. Do. Biu

Do. Do.

nucleus from the group consisting of benzene and phenyl pyrazolone, Z has a single nucleus from the group consisting of beta-naphthol, l-phenyl- 3- methyl-5-pyrazolone, meta-tolylene diamine, acetoacet-arylide, and Y is one or more of the group consisting of hydrogen, alkyl, alkoxy, halogen, carboxy, and sulfonic acid.

3. The compound representedin the form of a its free acid by the formula:

I Y in which aryl is one of the group consisting of benzene and alpha'naphthylamine and in which at least one aryl has a water-s'olubilizing substituent, E has a single nucleus from the group consisting. of benzene and phenyl-pyrazolone, Z

has a single nucleus from the group consisting of beta-naphthol, phenyl-pyrazolone, meta-tolylene-diamine, and acetoacet-arylide, and Y is one or more of the group consisting of hydrogen,

aikyl, alkoxy, halogen, carboxy, and sulfonic acid.

4. The process which comprises dyeing cellulose with a compound representedin the form ofbenzene and alpha-naphthylamine, at least one of the said aryls having a. water-solubilizing in which aryl is one of the group consisting of group from the class consisting of carboxylic acid and sulfonic acid, E is one of the group consisting of benzene and phenylpyrazolone, having a free amino group, and Y is at least one of the group consisting of hydrogen, alkyl, alkoxy, and halogen, diazotizing the color on the fiber, and coupling it to one of a groupof compounds consisting of beta-naphthol, 1-phenyl-3-methy1-5- pyrazolone, meta-tolylene-diamine and acetoacet arylide.

CHESTER W. HANNUM.

SWANIE S. ROSSANDER. 

